How to Lose Well - Coaching with Sid

If you know me, you know how much I hate losing.

I’m that friend who’s in it to win it.

For a long time, I believed it was what made me better.
That edge.
That drive.
That voice in my head that said, ‘Push harder. Do more. Win again.

But recently, something shifted.

It all started with a game of padel.

One day, after losing an easy match, I began noticing something…

The way I spoke to myself after losing a point?

It was Harsh. Critical. So judgemental.

And after I lost a game? My mood didn’t stay on the court.
It followed me — into conversations, into my home, into my energy.

In fact, my wife has a running joke

She says she can instantly tell whether I’ve won or lost.

Because on the days I lose — I’m more irritable, impatient, and hard on everything… and everyone.

When I started paying attention, I realized…

It wasn’t just about losing a game.

It was about what losing triggered inside me.

A belief that I had to earn my own self-respect through winning.

That my worth was only safe when I came out on top.

That realization cracked something open.

It made me wonder — what does it really mean to lose well?